Waterinsoluble azodyestuffs



Patented Sept. 11, 1934 1,73,013

UNITEDhSTATES PATENT 'tetee 1,973,013 I WATERINSOLUBLE A'zoDYEs'rUFFs Friedrich Muth, Leverkusen-I. G. Work; and August Modersohn, Cologne-Mulheim, Ger many, assignors to General Aniline -Works Inc., New York, N. Y., a corporation of Delaware v No Drawing. Application July 8, 1932, Serial No. 621,520. In Germany July 22, 1931 J 1:

12 Claims. 1 2 0-95 The present invention relates to waterinsoluof excellent 'fastnes's to boiling, chlorine and light ble dyestuffs, more particularly it relates to dyeis thus'obtained. e l stuffs which may be represented by the general The dyestufihas the following formula:'. I

formula: 5 55 I N a OH X y In an analogous manner "the diazot1zedy2- I wherein X means hydrogen or alkyl, such as aminodiphenylsulfone yields with;

methyl or ethyl, or alkoxy, such as methoxy or 2 -'-'hydroxynaphthalene'- 3 carboylamino -p ethoxy, Y stands for hydrogen; a halogen atom 4-chlorobenzene, an orange. j:

or analkoxy group, but X and Y beingdifierent 2 hydroxynaphthalene 3 carboylamino from each other, the azo group being attached to 4-methoxybenzene, a reddish-orange. 1 the benzene nucleus inthe position 0- or mwith 2 hydroxynaphthaleneiv- 3 carboylammo Z9 respect to the sulfone group. I 2'methoxy-4-ch1orobenzene, an oran Our dyestuffs are prepared in the usual man- 2 hydroxynaphthalene 3 carboylamino ner by diazotizing 2 -aminoor 3v-aminodiphenyl 2-methylbenzene, a scarlet. sulfone and coupling with a 2-hydroxynaphthoic 2 hydroiiynaphthalene 3 carboylamino 1 acid-arylamide of the general formula: 2'-methy1 Qz an qrange 175 2 "'-"hydroxynaphthalene e 3 carboylamino OH X 2'-methyli' methoxybenzene, a reddish-orange. 2 hydroxyn'aphthalene -"-3 '-carboy1amino O0NH 'Y 2'-ethoxybenzene; a-reddish orange-.-

2 hydroxynaphtha'tlene' 3 carboylamino 2- 80 wherein X and Y mean the same as stated above. ethylbenzene} a reddish-orange. r

The dyestuffs are, when produced in substance, Example 25-233 grams of Z-aminOd-iPheHyI SuI- generally orange p w er When pr uc d n he tone are diazotized'in the-usual manner; and lmto fibre according to the method of producing icethe diazo solution which has been neutralized by c lo s, th y yi d e ally oran shades of goo the addition of sodium acetate there is introduced 85 fastness properties. an aqueous soda alkaline solution prepared fr'om The invention is illustrated by the following 307 grams of 2-hydroXyn Dl r y examples, without being limited thereto; a ino-2-methyl-4-methoxybenzene. Coupling Example 1.-50 grams of cotton yarn are treatis soon complete, the orange-red precipitate 1s ed for half an hour in 1 litre of a bath containing filtered, washed and dried. 9o 5 grams of 2-hydroXy-naphthalene-3-carboxyl- Example 3.- grams of cotton yarn are treatamino-2-methoxybenzene, 10 cos. of aqueous ed for 1 hour in 1 litre of a bath containing 3 caustic'soda lye of 38 B. and 10 cos. of Turkey grams of 2-hydroxynaphthalene 3 carboylaminored oil. Then the yarn is squeezed and intro- 2-methyl-4-ch1orobenzene, 6iccs.; of Turkey red duced for half an hour into a diazo solution preoil and 9 cos. of an aqueous caustic soda lye of pared in the usual manner and containing the 38 B. -Then the yarn is squeezed and introdiazo compound from 2,35 grams of Z-aminodiduced for-half an hour into a diazo solution phenylsulfone. The yarn is then rinsed, soaped prepared inthe usual manner and containing a 50 at the boil and dried. A vivid yellowish-orange diazo-solution prepared from 2.35 grams of 3.-

soaped at the boil and dried. A clear orange of excellent fastness to boiling, chlorine and when produced on the fibre, orange shades of excellent fastness properties.

3. The azodyestufi of the following formula:

light is thus obtained.

The dyestuif has the following formula: mso I N V v I 1 i d OH 00m on OH; 0 ONH- C v V yielding, when produced on the fibre, vivid yellowish-orange shades of excellent fastness to boiling, In an analogous manner the diazotized 3- chlorine and taminodiphenylsulfone yields ith; 4. The 'azodyestufi of the following formula:

2 hydroxynaphthalene- 3 carboylamino -4'- 1 ohlorobenzene, an orange; S02* 2 hydroxynaphthalene 3 carboylamino -4'- methoxybenzene, a brownish-orange. g, x

2 hydroxynaphthalene 3 carboylamino- -2-'- V N methoxybenzene, a reddish-orange.

2 hydroxynaphthalene 3 carboylamino '2- methoxy-4-chlorobenzene, a reddish-orange.

2 hydroxynaphthalene 3 carboylamino -2' methylbenzene, a reddish-orange.

2 hydroxy'naphthalene 3 carboylarnino -2- methyl-4'-methoxybenzene, a reddish-orange.

2 hydroxynaphthalene 3 carboylamino -2'- ethoxybenzene, a reddish-orange.

2 hydroxynaphthlalene '3 carboylamino 2- ethylbenzene, a reddish-orange.

Example 4.233 grams of 3-aminodiphenylsulfone are diazotized and coupled with 277 grams I of 2 hydriaxynaphthalene 3 -c'arboylamino-2 E methylbenzene, as described in Example 2. An N z orange-red pigment is thus obtained.

We claim: OH x V 115 1 waterinsoluble azodyestuffs of the general I O p i wherein X stands for hydrogen or alkyl, Y stands g i p forhydrogen or chlorine, but X and Y being N different from each other, yielding, when produced 0 g E 10o -oo nngo' o om yielding, when produced'on the fibre, vivid yellowish-orange shades of excellent fastnes's to boiling, chlorine and light. l

5. Waterinsoluble azodyestufis of the general formula: Y I

Y on the fibre, orange shades of goodfastness properties.

OH x The az odyestuif of the'following formula: 00-,NH- Y I wherein X stands for hydrogen, alkyl or, alkoxy, 1 Y stands for hydrogen, alkoxy or a halogen atom, but X and Y being different from each other, the 13o azo group being attached to'the benzene nucleus *OH in the position 0- or mwith respect to the sul- (I fone group, yielding, when produced on the fibre, CO NI.I V I generally orange shades. I

. yielding, when produced on the fibre, clear orange Watermsoluble azodyesmfis of general shades of excellent fastness to boiling, chlorine formula: and light.

a so 7. Fibre dyed with a dyestuffas claimed in P Y claim 1.

N 8. Fibre dyed with a dyestuffjas claimed in H v Clal1n2. r 9. Fibre dyed with the claim3;

10. Fibre dyed with the dyestuff as claimed in claim 4.

11. Fibre dyed with a dyestuiT as. claimed in claim 5. 3

12. Fibre dyed-with the dyestuff as claimed in claim 6. y l P 140 dyestuif as claimed in oo NH- 4 wherein X stands for alkyl or alkoxy, Y stands for hydrogen, alkoxy or chlorine insuch a manner that X is not identical with Y and .Y stands for hydrogen in case X stands for alkoxy, yielding,

FRIEDRICH 'MUTH AUGUST MODERSOHN. 

